Deadspin associate editor Rick Chandler made a rather surprising confession to us the other day, and we demanded he write about it. So he now has the floor.

Trivia question: At the time that Marty Schottenheimer last won an NFL playoff game, Tom Brady was being coached by ...

Answer: Me.

And if that tidbit isn't enough to get Schottenheimer fired, nothing is. A friend called over the weekend to remind me that, during that cold, petulant January in 1991, Brady was playing for the Junipero Serra High (San Mateo, Calif.) freshman basketball team where I was a coach. Now it can be told; the school that gave us Barry Bonds, Lynn Swann and Gregg Jefferies was the site of my first coaching gig. And we were all sure that Brady was destined for great things in basketball.

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Football? He had played quarterback for Serra's freshman team that went 0-8, taking maybe a half-dozen snaps the entire season as the backup. You think Brady is slow now? He was glacial then. The man who replaced Drew Bledsoe couldn't, in his freshman year, rise above Kevin Krystofiak (currently a local insurance broker) on the depth chart. Back then we actually thought that his dominant sport would be baseball, where he was a catcher (in fact he was taken in the 18th round of the draft by the Montreal Expos following his senior year). Although he was the starting quarterback by the time he reached the varsity, he showed little of the three-Super Bowl promise that was to come. To my recollection, none of his Serra teams even made the playoffs.

But here's the thing. You knew, somehow, that Brady would make it. He was just too smart, too positive, and loved football too much. You rarely use the word destiny when dealing with teenage athletes, but Brady had that vibe. He was the kid who was always smiling. Even as a senior he would see me around campus and call out my name, and, for the record, it's not usually cool for an upperclassman to acknowledge their old freshman coaches. Reminds them of humbler times, like the football season when they were 0-8.

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But the Serra freshman basketball team? We were 9-3 and took a league co-championship. Who would have though then that Tommy Brady would go on to fame with a small role in the film Stuck On You? Crazy world.

By the way; my friend's math was a little off. Schottenheimer last won a playoff game in 1993 (Chiefs 28, Oilers 20), when Brady would have been a high school junior. By then I was coaching Dan Serafini on the freshman squad. Um, notice how none of these guys went on to play basketball? — RC

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(Ed. Note: Deadspin editor Will Leitch feels obliged to point out that in 1991, he was a sophomore in high school. He was not coached by Rick Chandler.)